US3071596A - Dihydrodibenzoxazepines - Google Patents
Dihydrodibenzoxazepines Download PDFInfo
- Publication number
- US3071596A US3071596A US90232A US9023261A US3071596A US 3071596 A US3071596 A US 3071596A US 90232 A US90232 A US 90232A US 9023261 A US9023261 A US 9023261A US 3071596 A US3071596 A US 3071596A
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- US
- United States
- Prior art keywords
- dihydrodibenz
- lower alkyl
- ketone
- oxazepin
- piperazyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/16—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D267/18—[b, e]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
Definitions
- the therapeutically active compounds of this invention include dihydrodibenzoxazepines of the general formula:
- A is a lower alkylene radical
- B is a basic saturated nitrogen-containing radical of less than twelve carbon atoms
- R and R are the same or different and represent hydrogen, halogen, lower .alkyl, lower alkoxy, trifluoromethyl, trifiuorornethylmercapto, trifluoromethoxy or N,N-dimethylsulfonamido.
- suitable radicals represented by the symbol B are: amino; (lower alkyl)amino; di(lower alkyl)amino; (hydroxy lower alkyl)arnino; di(hydroxy-lower alkyl)amino; and basic saturated 5 to 6 membered N-heterocyclic radicals of less than twelve carbon atoms, as exemplified by piperidyl [i.e., piperidino, Z-piperidyl, 3-piperidyl and 4-piperidyl]; (lower alky1)piperidyl [e.g., 2, 3, or 4-(lower alkyl) piperidino 0r 2, 3, or 4-(N-lower alkyl)piperidyl]; di-
- (lower alkyl)-piperidyl [e.g., 2,4-, 2,5-, or 3,5-di(lower alkyl)piperidino, or 2, 3, or 4-(N-lower alkyl)-2, 3, or 4- (lower alkyl)piperidyl]; (lower alkoxy)piperidyl; pyrrolidyl; (lower -alkyl)pyrrolidyl; di(lower alkyl)pyrrolidyl; (lower alkoxy)pyrrolidyl; morpholinyl [i.e., morpholine, Z-morpholinyl and 3-morpholinyl]; (lower alkyl)morpholinyl; di(lower alk-yl)rnor-pholinyl; (lower alkoxy)m'orpholinyl; thiamorpholinyl; (lower alkyl)thiamorpholinyl; di(lower alkyUthiamorpholinyl;
- lower alkyl, lower alkoxy, and lower alltylene include both straight and branched chain radicals of less than eight carbon atoms.
- the particularly preferred com-pounds are those wherein A is a lower alkylene radical of two to three carbon atoms (i.e., ethylene, trimethylene-1,3, and propylenel,2); B represents a di(lower alkyl)amino radical, an N -(lower alkyl)piperazino radical, an N -(2-hydroxyethyl)piperazino radical, or an N -(2-acetoxyethyl)piperazino radical, and R and R are hydrogen.
- salts of the dihydrodibenzoxazepines those coming within the purview of this invention include the acidaddition salts, particularly, the non-toxic acid-addition salts.
- Acids useful for preparing the acid-addition salts include, inter alia, inorganic acids, such as the hydrohalic acids (e.g., hydrochloric and hydrobromic acid), sulfuric acid, nitric acid and phosphoric acid, and organic acids, such as oxalic, maleic, tartaric, citric, acetic and succinic acid.
- the compounds of this invention are therapeutically active compounds which are utilizable both as atar-actic agents, and thus may be used in the treatment of depressed psychotic states, and an antihistamines. For these purposes they may be administered orally or parenterally in conventional dosage forms such as tablets, capsules, in-
- EXAMPLE 7 Dimethylaminoeflzyl 3,7-Dichlor0-5,1J-Dihydrodibenz [1,4] Oxazepirz-S-Yl Ketone Following the procedure of Example 1, but substituting an equivalent amount of 3,7-dic-hloro-5,1l-dihydrodibenz [b,e] [1,4] oxazepine for the 5,11-dihydrodibenz [b,e] [1,4] oxazepine in step a, Z-dimethylarninoethyl 3,7- dichloro-5,1l-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone is obtained.
- N- (Z-hydroxyethyl piperazine, N- Z-acetoxyethyl) piperazinc, or N-(Z-hydroxyethoxyethyl)piperazine for the dimethylamine in step b of Example 1, 2-[N -(2-hydroxyethyl)piperazino]ethyl 5,1l-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone, 2-[N -(Z-acetoxyethyl)piperazino] ethyl 5,11-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone, and 2- [N 2-hydroxyethoxyethyl piperazino] ethyl 5,11- dih-y-drodibenz [b,e] [1,4] oxazepin-S-yl ketone are obtained respectively.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
United rates Pattit @fificei Patented Jan. 1, 1963 This invention relates to new basically substituted dihydrodibenzoxazepines (and their salts) having valuable therapeutic properties, processes for the preparation thereof, and new intermediates useful in such processes.
The therapeutically active compounds of this invention include dihydrodibenzoxazepines of the general formula:
wherein A is a lower alkylene radical, B is a basic saturated nitrogen-containing radical of less than twelve carbon atoms, and R and R are the same or different and represent hydrogen, halogen, lower .alkyl, lower alkoxy, trifluoromethyl, trifiuorornethylmercapto, trifluoromethoxy or N,N-dimethylsulfonamido. Among the suitable radicals represented by the symbol B are: amino; (lower alkyl)amino; di(lower alkyl)amino; (hydroxy lower alkyl)arnino; di(hydroxy-lower alkyl)amino; and basic saturated 5 to 6 membered N-heterocyclic radicals of less than twelve carbon atoms, as exemplified by piperidyl [i.e., piperidino, Z-piperidyl, 3-piperidyl and 4-piperidyl]; (lower alky1)piperidyl [e.g., 2, 3, or 4-(lower alkyl) piperidino 0r 2, 3, or 4-(N-lower alkyl)piperidyl]; di-
(lower alkyl)-piperidyl [e.g., 2,4-, 2,5-, or 3,5-di(lower alkyl)piperidino, or 2, 3, or 4-(N-lower alkyl)-2, 3, or 4- (lower alkyl)piperidyl]; (lower alkoxy)piperidyl; pyrrolidyl; (lower -alkyl)pyrrolidyl; di(lower alkyl)pyrrolidyl; (lower alkoxy)pyrrolidyl; morpholinyl [i.e., morpholine, Z-morpholinyl and 3-morpholinyl]; (lower alkyl)morpholinyl; di(lower alk-yl)rnor-pholinyl; (lower alkoxy)m'orpholinyl; thiamorpholinyl; (lower alkyl)thiamorpholinyl; di(lower alkyUthiamorpholinyl; (lower alkoxy)thia-morpholinyl; piperazyl; (lower alkyl)piperazyl (e.g., N -met-hylpiperazino); di(lower -alkyl)piperazyl; (lower alkoxy)piperazyl; (hydroxy-lower alkyl) piperazyl [e.g., N -(2-hydroxyethyl)piperazino]; (lower alkanoyloxyalkyl)piperazyl [e.g., N (2 acetoxyethyl) piperazino]; (hydroxy-lower alkoxy-lower alkyl)piperazyl [e.g., N -(Z-hydroxyethoxyethyl)piperazino]; and (car bo-lower alkoxy)piperazyl [e.g., (2carbomethoxy, carboethoxy, or carbopropoxy)piperazino]. The terms lower alkyl, lower alkoxy, and lower alltylene, as employed herein, include both straight and branched chain radicals of less than eight carbon atoms. The particularly preferred com-pounds are those wherein A is a lower alkylene radical of two to three carbon atoms (i.e., ethylene, trimethylene-1,3, and propylenel,2); B represents a di(lower alkyl)amino radical, an N -(lower alkyl)piperazino radical, an N -(2-hydroxyethyl)piperazino radical, or an N -(2-acetoxyethyl)piperazino radical, and R and R are hydrogen.
As to salts of the dihydrodibenzoxazepines, those coming within the purview of this invention include the acidaddition salts, particularly, the non-toxic acid-addition salts. Acids useful for preparing the acid-addition salts, include, inter alia, inorganic acids, such as the hydrohalic acids (e.g., hydrochloric and hydrobromic acid), sulfuric acid, nitric acid and phosphoric acid, and organic acids, such as oxalic, maleic, tartaric, citric, acetic and succinic acid.
The compounds of this invention are therapeutically active compounds which are utilizable both as atar-actic agents, and thus may be used in the treatment of depressed psychotic states, and an antihistamines. For these purposes they may be administered orally or parenterally in conventional dosage forms such as tablets, capsules, in-
- jectables or the like by incorporating the appropriate dose of the compound with carriers according to accepted pharmaceutical practice.
The compounds of this invention are prepared by the process of this invention which is shown in the following equation, wherein R, R, A and B are as hereinbefore defined:
application, Serial No. 90,225, filed on even. date here with. These starting materials are treated with a basically substituted lower alkanoyl halide of the formula: B-ACO halide, wherein B and A are as hereinbefore defined, the reaction preferably being conducted in the presence of a basic condensation reagent, such as sodium hydride, to yield the final products of this invention. The same compounds can alternatively be prepared in two steps, by first reacting with a halo (lower alkanoyl) halide of the formula: (halo)-ACO halide and then with a base of the formula: BH. To prepare the acid-addition salts, the resulting base is treated with the desired acid in the usual manner.
The following examples illustrate the invention (all temperatures being in Centigrade).
EXAMPLE .1
Z-Dimethylamr'noethyl 5,1l-Dihydrodibenz [b,e] [1,4] Oxazepin-S-Yl Ketone (a) Preparation 0) Z-chloroethyl 5,11-dihydrodibenz [b,e] [1,4] 0xazepin-5-yl ketone.-A mixture of 9.0 g. of 5,11-dihydrodibenz [b,e] [1,4] oxazepine, 11.7 g. of l3-chloropropionyl chloride and 150 ml. of dry toluene is refluxed for four hours, treated with Darco, filtered, and concentrated to dryness to leave a gummy residue weighing about 1 0.8 g. The gum crystallizes on drying in vacuo and after recrystallization from hexane melts at about 98-99".
(h) Preparation of Z-dimethylaminoethyl 5,11-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ket0ne.A mixture of 10.8 g. of 2-chloroethyl 5,11-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone, 18.0 g. of anhydrous dimethylamine and 50 ml. of toluene is heated in a sealed tube at 98 for 24 hours. The reaction mixture is then fil= tered, the filtrate is concentrated to dryness, and the oily residue dissolved in 100 ml. of ether. The ether solution is extracted with 100 ml. of 5% aqueous hydrochloric acid, the extract made alkaline and the base reextracted with ether. After drying, the ether is removed by distillation and the residue recrystallized three times from a very small amount of diisopropyl ether to give about 5.0 g. of product, M.P. about 78.5-80.0".
EXAMPLE 2 Z-Diethylaminoethyl 5,11-Dihydrdibenz [b,e] [1,4] Oxazepin-S-Yl Ketone Following the procedure of Example 1 but substituting an equivalent amount of diethylamine for the dimethylamine in step b, Z-diethylaminoet-hyl 5,11-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone is obtained.
EXAMPLE 3 Z-Dimethylaminoethyl 5,11-Dihydr0dibenz [b,e] [1,4] Oxazepin-S-Yl Ketone Hydrochloride To a solution of 5.92 g. of 2-dimethylaminoethyl 5,1-1- dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone in 25 ml. of anhydrous ether is added 0.75 g. of hydrogen chloride in 10 ml. of anhydrous ether. The precipitated solid is filtered, dried and recrystallized from acetonitrile-ether to give Z-dimethylaminoethyl 5,11-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone hydrochloride.
EXAMPLE 4 Z-Dimethylaminoethyl 3-Chl0ro-5,Z1-Dihydrodibenz [b,e] [1,4] Oxazepin-S-Yl Ketone Following the procedure of Example 3, but substituting an equivalent amount of 3-chloro-5,ll-dihydrodibenz [b,e] [1,4] oxazepine for the 5,11-dihydrodibenz [b,e] [1,4] oxazepine in step a, Z-dimcthylaminoethyl 3-chloro- 5,11-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone is obtained.
EXAMPLE 5 Z-Dimethylaminoethyl 3- Trifluorom ethyl) -5,1 l-Dyhydrodibenz [b,e] [1,4] 0xazepin-5-Yl Ketone Following the procedure of Example 1, but substituting an equivalent amount of 3-(trifluoromet-hyl)-5,1l-dihydrodibenz [b,e] [1,4] oxazepine for the 5,11-dihydrodi benz [b,e] [1,4] oxazepine for the 5,11-dihydrodibenz [b,e] [1,4] oxazepine in step a, Z-dimethylaminoethyl 3-(trifluoromethyl)-5,11-dihydrodibenz [b,e] [1,4] oxa- Zepin-S-yl ketone is obtained.
Similarly, by substituting an equivalent amount of 3-(trifluoromethoxy)-5,11-dihydrodibenz [b,e] [1,4] oxazepine, 3-(trifluoromethylmercapto -5, l l-di'hydrodibenz [b,e] [1,4] oxazepine or 3-(N,N-dimethylaminosulfonyl)- 5,11-dih-ydrodibenz [b,e] [1,4] oxazepine for the 5,11- dihydrodibenz [b,e] [1,4] oxazcpiue in step a, Example 1, Z-dimethylaminoethyl 3-(trifluoromethoxy) -5,1 l-dihydrodibenz [b,e] [1,4] ox-azepin-S-yl ketone, Z-dimethylaminoethyl 3 (trifluoromethylmercapto)-5,1l-dihydrodibenz [b,e] [1,4] oxazepin-S-yl and Z-dimethylaminoethyl 3-(N,N-dimethylaminosulfonyl) -5,1 l-dihydrodibenz [b,e] [1,4] oxazepin-5-yl are prepared, respectively.
EXAMPLE 6 2-D imethylaminoethyl 7-M ethyl-5 ,1 1 -Dihydr0dibenz [b,e] [1,4] Oxazepin-5-Yl Ketone Following the procedure of Example 1, but substituting an equivalent amount of 7-methyl-5,1l-dihydrodibenz [b,e] [1,4] oxazepine for the 5,11-dihydrodibenz [b,e] [1,4] toxazepine in step a, Z-dimethylarninoethyl 7-methyl- 5,11-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone is obtained.
EXAMPLE 7 2 Dimethylaminoeflzyl 3,7-Dichlor0-5,1J-Dihydrodibenz [1,4] Oxazepirz-S-Yl Ketone Following the procedure of Example 1, but substituting an equivalent amount of 3,7-dic-hloro-5,1l-dihydrodibenz [b,e] [1,4] oxazepine for the 5,11-dihydrodibenz [b,e] [1,4] oxazepine in step a, Z-dimethylarninoethyl 3,7- dichloro-5,1l-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone is obtained.
4 EXAMPLE 8 Dimethylaminomethyl 5,11-Dihydrodibenz [b,e] [1,4] Oxazepin-5-Yl Ketone Following the procedure of Example 1, but substituting an equivalent amount of chloroacetyl chloride for the fl-chloropropionyl chloride in step a, dimethylaminomethyl 5,11-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone is obtained.
EXAMPLE 9 2- (N -Methy lpiperazino) Ethyl 5 ,1 1 -D ihydrodibenz [b, [1 4 Oxazepin-S-Yl Ketone Following the procedure of Example 1, but substituting an equivalent amount of N-methylpiperazine for the dimethylamine in step b, 2-(N -methylpiperazino)ethyl5,11- dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone is ob tained.
Similarly, by substituting an equivalent amount of N- (Z-hydroxyethyl piperazine, N- Z-acetoxyethyl) piperazinc, or N-(Z-hydroxyethoxyethyl)piperazine for the dimethylamine in step b of Example 1, 2-[N -(2-hydroxyethyl)piperazino]ethyl 5,1l-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone, 2-[N -(Z-acetoxyethyl)piperazino] ethyl 5,11-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone, and 2- [N 2-hydroxyethoxyethyl piperazino] ethyl 5,11- dih-y-drodibenz [b,e] [1,4] oxazepin-S-yl ketone are obtained respectively.
This invention may be variously otherwise embodied Within the scope of the appended claims.
What is claimed is:
1. A compound selected from the group consisting of bases of the formula wherein A is lower alkylene, B is selected from the group consisting of amino, (lower alkyl)amino, di(lower a1- kyl)amino, (hydroxy-lower alkyl)amino, di(hydroxylower alkyl)amino, piperidyl, (lower alkyl).piperidyl, di(lower alkyl)piperidyl, (lower alkoxy)piperidyl, pyrrolidyl, (lower alkyl)pyrrolidyl, di(lower a1kyl)pyrrolidyl, (lower alkoxy)pyrrolidyl, morpholinyl, (lower alkyl)morpholinyl, di(lower alkyl)morpholinyl, (lower alkoxy)morpholinyl, thiamorpholinyl, (lower alkyl)thiamorpholinyl, di(lower alkyl)thiamorpholinyl, (lower alkoxy)thiamorpholinyl, piperazyl, (lower alkyl)piperazyl, di(lower alkyl)piperazyl, (hydroxy-lower a1kyl)piperazyl, (lower alkanoyloxyalkyl)piperazyl, (hydroxy-lower alkoxy-lower alkyl)piperazyl, and (carbo-lower alkoxy) piperazyl and R and R are each selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, trifluoromethyl, trifluoromethylmercapto, trifluoromethoxy and N,N-dimethylsulfonamido and non-toxic acidaddition salts thereof.
2. Di(lower alkyl)amino(lower alkyl) 5,11-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone.
3. A non-toxic acid-addition salt of the compound of claim 2.
4. 2 dimethylaminoethyl 5,11-dihydrodibenz [b,e] [1,4] oxazepin-S-yl ketone.
5. A compound of the formula [I O A (halide) C Hz 0 wherein A is lower alkylene and R and R are each se- 5 6 lected from the group consisting of hydrogen, halogen, 7. Z-chloroethyl 5,11-dihydrodibenz [-b,e] [1,4] oxazelower alkyl, lower alkoxy, trifluoromethyl, trifluoromethpin-S-yl ketone.
ylmercapto, trifiuoromethoxy and N,N-dimethylsulfon- References Cited in the file of this patent amido.
6. Chloroflower alkyl) 5,11-dihydrodibenz [b,e] [1,4] 5 UNITED STATES PATENTS Q a epi11 5-y1 ketone Hafiiger et a1 .Tan. 12,
Claims (1)
1. A COMPOUND SELECTED FROM THE GROUP CONSISTING OF BASES OF THE FORMULA
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90232A US3071596A (en) | 1961-02-20 | 1961-02-20 | Dihydrodibenzoxazepines |
| GB5465/62A GB951839A (en) | 1961-02-20 | 1962-02-13 | Dihydrodibenzoxazepines |
| BR136461/62A BR6236461D0 (en) | 1961-02-20 | 1962-02-16 | PROCESS FOR THE PREPARATION OF DI-HYDRO-DI-BENZO-XAZEPINES |
| FR897814A FR1847M (en) | 1961-02-20 | 1962-05-17 | New dihydrodibenzoxazepines and their salts. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90232A US3071596A (en) | 1961-02-20 | 1961-02-20 | Dihydrodibenzoxazepines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3071596A true US3071596A (en) | 1963-01-01 |
Family
ID=22221886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US90232A Expired - Lifetime US3071596A (en) | 1961-02-20 | 1961-02-20 | Dihydrodibenzoxazepines |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3071596A (en) |
| BR (1) | BR6236461D0 (en) |
| GB (1) | GB951839A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133936A (en) * | 1961-02-20 | 1964-05-19 | Olin Mathieson | Dihydrodibenzoxazepines |
| US3188321A (en) * | 1962-08-08 | 1965-06-08 | Olin Mathieson | Dihydrodibenzothiazepines |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2666051A (en) * | 1954-01-12 | N-acyl derivatives of iminodibenzyl |
-
1961
- 1961-02-20 US US90232A patent/US3071596A/en not_active Expired - Lifetime
-
1962
- 1962-02-13 GB GB5465/62A patent/GB951839A/en not_active Expired
- 1962-02-16 BR BR136461/62A patent/BR6236461D0/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2666051A (en) * | 1954-01-12 | N-acyl derivatives of iminodibenzyl |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133936A (en) * | 1961-02-20 | 1964-05-19 | Olin Mathieson | Dihydrodibenzoxazepines |
| US3188321A (en) * | 1962-08-08 | 1965-06-08 | Olin Mathieson | Dihydrodibenzothiazepines |
Also Published As
| Publication number | Publication date |
|---|---|
| GB951839A (en) | 1964-03-11 |
| BR6236461D0 (en) | 1973-05-31 |
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